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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H26N6O
Molecular Weight 354.4493
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SELICICLIB, (S)-

SMILES

CC[C@@H](CO)NC1=NC2=C(N=CN2C(C)C)C(NCC3=CC=CC=C3)=N1

InChI

InChIKey=BTIHMVBBUGXLCJ-HNNXBMFYSA-N
InChI=1S/C19H26N6O/c1-4-15(11-26)22-19-23-17(20-10-14-8-6-5-7-9-14)16-18(24-19)25(12-21-16)13(2)3/h5-9,12-13,15,26H,4,10-11H2,1-3H3,(H2,20,22,23,24)/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula C19H26N6O
Molecular Weight 354.4493
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

(S)-Seliciclib is enantiomer of the potent cyclin-dependent kinase (CDK) inhibitor Roscovitine. Roscovitine (racemic mixture) is an inhibitor of cell cyclin-dependent kinase (CDK)-2, CDK-4 and CDK-5, which are upregulated in stress conditions inducing apoptosis. (S)-Seliciclib potently inhibits Cyclin-dependent kinase 1. In vivo studies in rabbits demonstrated that both isomers (R- and S-) significantly reduce intraocular pressure (IOP). However, S- isomer was superior to R- isomer in lowering IOP and providing protection to retinal ganglionic cells.

CNS Activity

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
550.0 nM [IC50]
570.0 µM [EC50]
350.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

New Zealand White (albino) rabbits were used for activity evaluation. (S)-Seliciclib Was suspended in 4% (w/v) polyethylene glycol (PEG) 4000 at a concentration of 0.1%. Drug solution (50 mkL) was topically administered in the left eyes.
Route of Administration: Topical
The cultured retinal ganglion cell (RGC-5) line were used for activity evaluation. Cultures were maintained at 37 C in a humidified atmosphere of 95% air and 5% CO2. The RGC-5 cells were passaged by trypsinization every 3–4 days. The oxygen–glucose deprivation (OGD)-induced cell death assay involved seeding the cells at a density of 2 x 10^3 cells per well into 96-well plates, followed by incubation in a humidified atmosphere of 95% air and 5% CO2 at 37 C for 24 h. The OGD stress was induced by washing the cells with glucose-free DMEM (Invitrogen, Carlsbad, CA, USA) and then placing them in the same medium in a hypoxic incubator (94% N2, 5% CO2, and 1% O2) for 4 h. At the end of the OGD period, glucose solution and FBS were added at final concentrations of 4.5 mg/mL and 1%, respectively, and the cultures were returned to the incubator for an additional 16 h at the regular atmospheric oxygen level (reoxygenation). The roscovitine R-isomer or S-isomer ((S)-Seliciclib) was added to the culture immediately after replacement of the culture medium. At the end of this culture period, the cell viability was measured.
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:00:29 GMT 2023
Edited
by admin
on Sat Dec 16 10:00:29 GMT 2023
Record UNII
8C43G94891
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SELICICLIB, (S)-
Common Name English
SELICICLIB (2S)-FORM [MI]
Common Name English
(S)-SELICICLIB
Common Name English
1-BUTANOL, 2-((9-(1-METHYLETHYL)-6-((PHENYLMETHYL)AMINO)-9H-PURIN-2-YL)AMINO)-, (2S)-
Systematic Name English
Code System Code Type Description
FDA UNII
8C43G94891
Created by admin on Sat Dec 16 10:00:29 GMT 2023 , Edited by admin on Sat Dec 16 10:00:29 GMT 2023
PRIMARY
PUBCHEM
6603989
Created by admin on Sat Dec 16 10:00:29 GMT 2023 , Edited by admin on Sat Dec 16 10:00:29 GMT 2023
PRIMARY
MERCK INDEX
m9849
Created by admin on Sat Dec 16 10:00:29 GMT 2023 , Edited by admin on Sat Dec 16 10:00:29 GMT 2023
PRIMARY Merck Index
CAS
186692-45-5
Created by admin on Sat Dec 16 10:00:29 GMT 2023 , Edited by admin on Sat Dec 16 10:00:29 GMT 2023
PRIMARY